


Pretty Please with a Pie on Top?

by nameless_novelist



Category: Supernatural
Genre: Alternate Universe - High School, Bisexual Dean Winchester, Fluff and Humor, Happy Ending, M/M, Pining Castiel (Supernatural), Slow Build
Language: English
Status: In-Progress
Published: 2021-01-04
Updated: 2021-01-04
Packaged: 2021-03-14 01:28:39
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,291
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28538118
Author URL: https://archiveofourown.org/users/nameless_novelist/pseuds/nameless_novelist
Summary: Normally, the most logical thing to do when your best friend ask you out is to turn them down. Things would become way too awkward when you break up with them – it’d result in not only losing your date but also your best friend. However, when pie comes into the equation and it's not just any pie but a pie from Gabriel’s (Yes, that’s the name of a bakery), Dean's resolution wavers.
Relationships: Castiel/Dean Winchester
Kudos: 28





	Pretty Please with a Pie on Top?

DAY 0

“Dean, what would you say if I asked you out on a date?”

For a moment, Dean doubted his ears because that couldn’t be what Cas had just said. Cas, a boy-next-door who soon became his best friend in school and is now his bestest friend. Well, he always corrected Dean by claiming that word “bestest” is grammatically incorrect, all the while making air quotation marks with his fingers. Dean didn’t bother correcting himself though, since he knew Cas quite liked that title.

When Cas coughed lightly to get his attention, Dean blinked and frowned at him. Right, he was yet to give an answer to him.

“Dude, is this a joke or something? Because if it is, it ain’t funny.”

Dean mentally crossed his fingers, hoping that Cas would look at him with wide eyes, like a deer caught in a headlight, and admit sheepishly it was just a stupid joke. Much to Dean’s disappointment, that didn’t happen.

“No, I can assure you that this is not a joke.”

“So you actually mean it?”

“Every word.”

The way Cas said those words solemnly like he was promising scout’s honor would have been pretty hilarious if it weren’t for the situation Dean had found himself in. Shit. He tried to come up with something to say, something that would hopefully steer them away from getting awkward with each other.

“Uh, then since when did you like me? How come I never knew?”

Great, this was definitely going to get him out of this sticky situation. Dean groaned inwardly as he waited for Cas to reply, half in resignation and half with curiosity as to what Cas might actually reply.

“There are a lot of things you don’t know about me, Dean. Besides I knew that you would freak out if I said-“

“Freak out? I'm not freaking out! I'm just, I’m just, you know, surprised.”

Disbelief was clearly written across his face but Cas agreed with Dean dryly, “Right.”

“So you want to date me, huh? Be my boyfriend and all that? Does that mean you wanna hold my hand or something?”

Desperate attempt to lighten the mood, Dean tried to turn this into a joke and wiggled his fingers for a good measure. Castiel simply looked up and rolled his eyes in exasperation.

“Something like that, yes. But I would like to take you out to dates as well. Watch movies, then go to a diner and-“

“Which is what we do all the time. Or at least, some of the times.”

This time Cas downright glared at Dean as he said with a hint of annoyance, “Will you let me finish my sentence or should I pause every once in a while?”

“Sorry, continue,” Dean coughed.

“-and take you back home and kiss you good night.”

“Oh, okay. So you’re one of those classic guys.” Even without looking up at Cas, Dean could almost hear his eyeballs rolling again. “Er, but Cas, don’t you think it's better if we just stay as friends?”

“No, I don't,” came a curt reply.

“I mean, you are my best friend, and if I suddenly date you-“

“I could bring you a pie every morning, fresh out of the bakery.”

“-and, what?” Dean was ready to give a big speech to Cas about why dating your best friend was a most horrible idea one could think of, but the sound of ‘pie’ had made him stop from rambling on.

“The pies from Gabriel’s, your favorite.”

“Cas, are you actually propositioning me with pies?”

Dean made an exaggerated gasp because he knew that Cas damn well knew how much Dean liked pies. You need any favor from Dean? Just bring him pie. Anyone who has ever heard of Dean knows that already.

Cas fidgeted nervously, while he sighed exasperatedly. “No, Dean. Well, maybe. Yes. But I don’t like to call it like that. I prefer... wooing.”

“Whatever helps you sleep at night, Cas. Y’know I really can't say no to that.”

It was true, all the argument that Dean had come up with seemed to have slipped off his mind, the second he heard that those pies would be from Gabriel’s – the pies that are second best to Mom’s.

“So I bring you a pie every day for a week and you, in turn, would be my date for a week. Do we have an agreement?” Cas looked at Dean with such hopefulness that he couldn’t say no. Damn Cas for being able to make a puppy face, which was like kryptonite to him.

“Yeah, sure. Wait, did you say for a week?”

Although he was still very much against the idea of dating his best friend, having a deadline to this whole “date” thing left a bitter aftertaste. Why this bothered him so much, however, Dean himself had no idea.

“Yes. Would that be a problem?”

“No, I just thought... you know what, it’s nothing. We have a deal.”

When Cas smiled beamingly at him, Dean smiled back at him out of habit. Dean had done some stupid things before and this is definitely going to go on that list later, but if Dean tried to keep things under control, it couldn’t actually go bad, right?

DAY 1

The next morning Dean had almost forgotten about their little deal until Cas handed him a box before getting in Baby, his beautiful ’67 Chevrolet Impala. Well, it wasn’t his per se – it was his Dad’s – but it was as almost as good as his, since he had seen his parents discuss quietly about getting a new car for themselves. Pushing that thought aside, he stared quizzically at the box.

“What’s this?”

“The pies, remember?”

“Oh.” He grimaced and he felt uneasy upon remembering about yesterday and Cas’ surprise confession. However, as soon as he opened the box, the intense aroma wafted toward him and he couldn’t help but swallow thickly, his earlier unease drifting away.

Perhaps it was the pie or perhaps it was just the habit but when Dean held the handle and drove off to school, they were already having a small talk about their classes today and fell into a comfortable silence afterward, as music blared between them.

When they finally arrived at school Dean dropped Cas off as usual, before finding a suitable parking place for his Baby. Dean carefully packed the pie inside his backpack and carried it across his shoulder. He decided that he definitely won’t walk out on Cas, especially not after he got a pie from him, just like he promised he would.

Maybe it was because he finally made up his mind, Dean blatantly ignored winks from a sexy quarterback that he’d been flirting with for weeks and turned a cute sophomore down when she asked him out.

“Is everything ok, Dean?”

Charlie slapped his back and looked up at him with a frown on her face.

“Huh, why d’you ask?”

“Dude, you suddenly stopped flirting around with everyone. You, Mr. I-hit-on-everyone-‘cause-I’m-bi.”

“I don’t hit on people. It’s the people who are hitting on me. ‘Sides can’t a guy take a break once in a while?”

Although Dean tried to brush it off, she just wagged her fingers at him. “Still something’s fishy. Very fishy.”

Thankfully a bell rang just then, saving him from further questions. He knew he couldn’t avoid Charlie for long and she could and would crack just about anything if she set her devious mind on it.

The classes went rather uneventful, maybe with a side note that Dean had paid more attention in class because he wasn’t flirting around with other students when he felt them gazing at him.

It was already lunchtime and as much as Dean couldn’t wait to indulge himself with the pies, he was dreading it, which was something new. Ask anyone, they would all say that Dean loves eating as much as he likes sex. And he likes sex a lot.

It’s just that he’d have to see Cas in lunch and he wasn’t sure how he should act in front of him. Should he simply treat him like nothing had happened? Should he flirt with him?

He almost yelped when Cas sneaked up behind him.

“Hello, Dean.”

“Dude, you really need to make some sound.”

“I just did.” Cas shrugged nonchalantly, but the corners of his mouth were shifting upwards by a fraction. Smug bastard.

They walked in silence toward Charlie, who was already sitting in their usual place.

“Um.. so, Cas, er, how was your day?” He asked as he took a seat, wincing at how awkward he sounded.

Charlie looked at him incredulously but before she could make a comment, Cas swooped in answered, “It's been going rather well. How about you?”

“Yeah, it's alright.”

“Dean, is there something wrong?”

Seeing Cas’ eyebrows furrowing, Dean waved his concern off like it was nothing. “Nothing. Everything's just peachy.”

“If you say so.”

During the rest of the lunch, Dean didn’t try to begin a conversation, only quipping in here and there.

After lunch, Castiel rushed off to go to Advanced Placement English in the other building, leaving Dean alone with Charlie and Charlie wasted no time to turn around and corner him.

“What, was that.”

“Nothing.”

“Did you guys have a fight or something?”

He considered his chance if he made a break from all this. Unfortunately, his chance looked pretty slim.

“Spill.”

He closed his eyes and rushed through his words. “I’m kinda seeing Cas?"

"Really? I can't believe you guys are finally going out! I thought it'd take decades for you to realize you are in love with each other... wait, what do you mean ‘kinda’?"

“Well, it’s more like a one-week trial. We are just seeing if it could work. I said it wouldn’t but hey, I’m at least getting pies out of this.”

“Winchester, you just said yes to get some pies?” Charlie looked at him as if she wanted to burst out into laughter or hit him on the shoulder. Probably both.

“They are good.”

“Dean, this isn’t some stupid dare that you can laugh about afterward!”

“I know,” Dean answered quietly, and he could see the fight draining out of Charlie. Charlie let out a huff before putting a hand on his shoulder and squeezing it gently.

“Oh, well. You know I love you Dean but if this goes wrong, I am definitely going to give you a hard time.”

“I know that too.”

“Hey, don’t worry too much. Now that I know what’s going on, I will just keep my eyes on the both of you.”

Dean wished that he could say that the rest of the day went smoothly. It hadn’t. Unlike the morning classes, Dean couldn’t focus at all in his afternoon classes. Not with the remark from Charlie echoing inside his head. Damn that girl for messing with his mind. Yeah, that must be it – she was trying to be a wing-woman by trying to set him up with Cas. Too bad for her, Dean thought, she’s just barking at the wrong tree if she thinks something will happen between them. Just because they are attached at the hip doesn’t mean they are joined together at everything.

Dean was in a sour mood, even when it was time for them to go back home. Cas must have noticed it like he always did, but he didn’t bring it up. In fact, even though Dean was fuming behind the wheel driving just a little over the speed limit, Cas stayed silent, save for the few glances he sent toward Dean’s direction.

When they arrived at Cas’ house, only then Dean was able to say something albeit in frustration. “Shit, I should’ve asked you if you wanted to go somewhere else.”

“Why? You always drive me home on Monday.”

“I don’t know, man. You could’ve wanted to do something else,” he grumbled.

Cas smiled slightly upon sensing Dean’s back to his normal self now. “If I did, I would have told you, Dean. See you tomorrow.”

Dean laid his forehead on the wheels for a while, watching Cas get inside his house. If a whole week is going to be like this, he wasn’t so sure if he’d last and keep everything just like it always had been and should be.

DAY 2

Apparently, Charlie seemed to be completely aboard with the little idea of hers and she slung her arms around Dean’s shoulder – or at least, tried to.

“So let me get this straight... well, none of us really are, ha, ha. But oh well. Have you never thought about Cas, you know, as boyfriend material?”

“Dude, there has to be a universal code written somewhere that says you never think of your best friend that way,” Dean scoffed, not even amused at Charlie for even suggesting such an idea in the first place.

“You know that’s what every protagonist says in a chick flick before they end up marrying their best friends, right? Come on, Dean, you of all the people should know better.”

It was typical of Charlie to tease him about watching chick flicks which was actually rude considering he never complained to her about being a nerd herself. Though he had to admit, she introduced him to some of the good stuff. Just to save face, Dean gave her an evil eye.

“You’re just generalizing chick flicks. And no, I‘ve never thought about him that way. He’s like my best friend.”

“Yeah, and I’m your best friend too and you-”

Ha, for once he could actually outsmart Charlie on a discussion. “See? Even though I’m bi, I don’t think of you that way. You’re like a sister I don’t want to have and he’s like a brother... I guess I’m ok with having?” Dean frowned because this was definitely not how his sentence should’ve ended.

“Wow, thank you. I feel so flattered,” Charlie placed her hand over her chest in an overly dramatic way. “But seriously, Dean, you talk about Cas like, I don’t know, like you’re his boyfriend.”

“I what?”

“I mean, whenever somebody asks Cas something, you are the one who answers for him.”

“I never do that. Like, when did I do that?”

Dean may have had a vague idea of what she was talking about but he decided to play dumb. Which Charlie didn’t buy at all.

“Like all the time? If I ask something like ‘hey, Cas. What did you do over the weekend?’ And you answer ‘oh, apparently he stayed up late reading Harry Potter but hey, now he can appreciate the Wizarding World’.”

“Yeah, but there’s no way you would’ve been okay with him saying ‘I was reading’, aren’t I right?” Dean huffed, knowing he was completely right about this.

“No need to get so defensive, jeez. Besides it’s not like Cas is any better.”

“Oh yeah?”

“Mm-hmm. He looks at you in the same way you look at your pies.”

After hearing a new bit of information, Dean honestly had no idea how he should feel about it. He knew that Cas stared at him but he figured that it was because he was a spacey guy.

This was why Dean was casually shifting his gaze toward Cas every now and then. He was lying on his bed right now, reading a book Charlie recommended him to read and Cas was sitting on the floor while leaning against Dean’s bed. He held a book Dean had forced him to read but every single time Dean’s gaze would meet Cas’. Dean realized, much to his chagrin, that Charlie was right on the spot. Cas’ stare was nothing like a look of fascination or awe. This was too intimate to Dean’s comfort.

“Cas, are you staring at me?”

“You didn’t have much problem with it before” Cas pointed out with a flat voice.

Dean scoffed, “Yeah, I heard that before.”

“From who?”

“Charlie.”

Cas let out a chuckle and talked low, “I always knew she was the smart one.”

“But how long?”

“Ever since we were kids.” Cas stared at him again, locking eyes with him. Dean tried to shift his eyes away but he found himself that he couldn’t.

Luckily, Sam barged inside his room just then and whatever moment that they had back there was broken.

”Hey, Cas. Are you gonna have dinner with us?” Sam asked enthusiastically.

Cas offered him a warm smile as he stood up and grabbed his bag. “No, I’ll be going home today. Have a nice evening, Sam.”

“You too, Cas!” Sam waved at him and ran back downstairs.

“And I’ll be seeing you tomorrow,” Cas looked at Dean – less intently this time – before he walked out of the room.

And for some reason, Dean remained lying down on his bed, needed a moment to clear his mind and to not let his mind drift off to think about those blue eyes.

DAY 3

“Have you ever found Cas attractive?”

Charlie took a seat right next to Dean and asked the most stupid question he’d ever heard.

“Well, it’s not that he’s unattractive. But I don’t exactly find him attractive, either.”

“Sure, but that’s not what you said last time. What did you say? Oh right, you said he was ‘devastatingly handsome’.”

“No, I didn’t. You’re just making stuff up,” Dean snorted.

“Yeah, remember when a waitress was flirting with him like a week ago? You said, quote, unquote, ‘My shy but devastatingly handsome friend here‘.”

Was she for real? “Well, that’s what a wingman do!”

“Fine, fine. Here’s what we are going to do. Just close your eyes and think of Castiel, ok? Not as Castiel, your bestie or whatever, but Castiel Novak, just a senior in our high school.”

“This is stupid,” he mumbled but he closed his eyes nonetheless.

“And shut your mouth until I say otherwise. Now describe how he looks like. Just, say, 10 sentences or so.”

“Uh, he’s- he’s got dark hair, blue eyes... Tell me why am I doing this?”

“To humor me. Go on.”

“He’s slightly shorter than me. Um, he always likes to wear collared shirts? And... nothing, I got jack squat.”

Dean sighed frustratedly before peeking his eyes open but Charlie was looking at him like she had all the time in the world and judging by her determined expression, she wasn’t going to let him bail from this.

“Then can I say he has really intense blue eyes?”

“Interesting. I will accept that too”.

“Okay then, well, he’s not skinny but still rather lanky? And oh, he has firm thighs. From all the running.”

Apparently, Charlie had meant it when she said he was supposed to say 10 sentences to describe Cas. Only after he gave her four more descriptions on Cas, did she let this drop. She didn’t bother explaining what she thought about it, though. She just hummed to herself, seemingly lost in her own mind.

Well, Dean decided that he wouldn’t bother worrying about their little talk, either. That’s why he was feeling quite okay when he was walking down the road with Cas by his side. Today was Walk-To-School Wednesday – a stupid ritual that Cas made up, saying a 30-minute walk couldn’t hurt once in a while.

Since the sidewalk was too small for two teenagers to walk side by side, Dean usually walked on the side of the road. Cas would always frown at him and tell him to get back up on the sidewalk but Dean easily waved him off, because he liked walking next to Cas. Even if they don’t really talk so much on the way. Just like now with Cas spacing out to who-knows-where and Dean kicking a few of the pebbles out of his way and beginning to hum Led Zeppelin songs under his breath.

It was that moment when a car driving at high speed was making a screeching sound as it halted and before he could react, Cas had gripped him tightly by his arms and pulled him onto the sidewalk. He barely heard the driver cursing at them and driving off because he was busy staring into the blue eyes.

Cas’ widened eyes were the only indication that he was startled by the near-accident. He didn’t even screw up his face in concentration as he single-handedly dragged Dean away from the road like he didn’t weigh anything.

“Well, that was hot.”

“Excuse me?”

Cas was looking at him funny and it took Dean a moment to realize that he had just spoken his thought out loud.

“What?” Somehow Dean managed to sound nonchalant enough, which he was more than pleased about.

“You said ‘Well, that was hot’. What was?” Cas tilted his head slightly to the right – a typical gesture he made when he was confused.

“Nothing!” Dean exclaimed, blanching at how his voice suggested the exact opposite, and then quickly elaborated his sentence. “Fine, uh, you see... I’m just feeling hot from the adrenaline rush or whatever.”

Cas didn’t look convinced at all but he did let the topic drop, which Dean was quite grateful for. Unfortunately, that meant that they had fallen into an uncomfortable silence. Dean said some random things to ease this tension but it seemed to have only backfired, as they exchanged rather awkward goodbyes before heading inside their homes.

DAY 4

Dean hadn’t had a wink of sleep last night. Well, that was him being a tad dramatic but he wasn’t lying about being unable to sleep very well. Even though he was lying on his bed, ready to go to sleep, his mind was floating off to a certain blue-eyed friend of his every so often. Which was exactly why he scowled at Charlie when he saw her in the morning.

“This is all your fault.”

Charlie’s lips twitched in amusement. “Don’t be so bitchy, Winchester. What exactly is my fault?”

“Ever since that, that weird question, I feel funny.”

“I sense that there’s something more to it. Come on, lay it on me so I can offer you some Jedi wisdom.”

“Right,” he drawled sarcastically, but he began to explain what had happened yesterday. And damn, it felt right to get it off his chest.

“Ok, so you are saying that you now feel hot and bothered by Cas?”

That was definitely not the point and Dean couldn’t help but groan in frustration. “No, Charlie. I’m saying that I shouldn’t be thinking the way Cas pulled me away from the car, er, hot.”

“There’s nothing wrong with that. We both know you kind of have a thing for manhandling,” Charlie shrugged indifferently.

“Yeah, but it’d kind of suck for Cas if someone told him ‘Look, I know you like-like me, but I don’t feel the same way. But hey, at least I think you are kinda hot’. So I want a better explanation as to why I suddenly find Cas... um, different.”

“Well, there’s something called suspension bridge effect.”

“A what?”

“You know how two people fall in love after they’ve survived an accident? That’s the psychological explanation for it. I mean, were you scared when the car was speeding toward you?”

Dean thought about it before answering, “Not really. Cas pulled me away before I even heard the car.”

“Then this can’t be the reason,” Charlie sighed. “And that means, whatever the reason is? It’s on you.”

“Shit.”

“Why are you so against going out with him anyway?”

“Easy, you should never start a romantic kind of relationship with your best friend.”

Charlie rolled her eyes as if she couldn’t believe what she’d just heard. “That’s not a good enough reason.”

“It is for me. If it goes down in flames, I’m gonna lose a boyfriend and my best friend all at once, y’know?”

“I’m pretty sure he’d still stay as your friend,” Charlie coaxed, her face morphing into a more sympathetic look.

Dean didn’t say anything, not even agreeing or disagreeing with her, and only raised one of his eyebrows passively. Which only resulted in angering Charlie.

“You are such a hypocrite, Dean, you know that? Because if you wanted to freak about how things may change with Cas, it’s too late for you to worry about it now. You should’ve done that before starting this ‘trial’ thing with him.”

Charlie stormed off, fuming, and Dean immediately felt bad about being a dick toward her. The truth was, he was just as lost as everyone else. It wasn’t exactly like he had time to think it through before saying “I’m in”. Dean didn’t regret his decision, though, since he knew if he could go back in time, he would make the same choice all over again.

You see, getting pie every day was just a cherry on top. And as much as Dean liked those sugar-sweet cherries on top of the ice cream, milkshake, cake, and all other kinds of desserts, those were just something extra – it was the dessert that really mattered. To him, the “cake” in their little arrangement was not having to see Cas’ crestfallen face.

Dean knew from the start he was only prolonging the inevitable but he wanted to delay giving an answer whether it be a yes or a no. His initial reaction had been actually to say no because saying yes was absurd when a) he didn’t feel any kind of attraction toward Cas and b) there was no way he’d date his best friend. However, he didn’t feel like saying no either because he never, ever was able to turn Cas down.

Today was Thursday and that meant him and Cas would chill out at his home after school. Although Dean was holding a book in his hand, the same book he had a hard time closing two days ago, he didn’t even bother opening it today. He was too busy staring at Cas to see if there were any other parts about his friend that he was attracted to.

After some close inspection Dean grudgingly admitted to himself that Cas was attractive. Not that the looks mattered much to Dean when he dated guys or girls but good looks didn’t hurt either. His piercing blue eyes and his nose, straight and refined, were just a few of the well-defined but nonetheless one of his best features. For example, his dark and disheveled hair was really soft and he could be sure about this since he used to play with it often before Cas stopped him from it.

Dean was lost in his thought until Cas suddenly closed his book, before sighing, “Dean, is there something on my face?”

“Nope,” Dean grinned cheekily at him, making sure to make a pop sound on the last syllable.

“Then why are you staring at me like that?”

Cas was frowning slightly and tilted his head to the side. And damn, did that look cute on him.

“I dunno. You stare at me all the time so you can’t tell me that I can’t.”

“I wasn’t going to.”

The light hit him just right then and it almost looked as if there were a halo above Cas. Which would have been quite fitting, considering his actual name – Castiel – was the name of an angel.

Great, now he was beginning to gushing over Cas like he was some sort of a lovesick teenage girl mooning over her crush. Dean groaned inwardly because this was definitely not how this “trial” date thing was supposed to go down.

DAY 5

On their way to school, with Dean driving Cas to school like always, Cas asked casually, “Dean, do you have any plans for today?”

“Not really, why?” Dean was more than confident in his driving skill and he glanced at Cas as he answered him.

“Eyes on the road, Dean.” Only when Dean complied grudgingly and kept his eyes on the road, Cas replied, “Then let’s go on a date. Today.”

Dean mentally patted himself on the back when he managed to put up a poker face. Well, there wasn’t no reason anything to be scared about, now, was there? Dean thought, trying to keep his anxiety minimum. He had been to more dates than Cas and he knew for a fact that Cas hadn’t had a single date. That, unfortunately, made Dean’s anxiety worse, since it meant that Dean was his first date.

“Dean.”

Cas’ voice snapped Dean out of his little spacing out.

“Huh?”

“Are you okay?”

Cas’ eyebrows knitted together in concern and Dean quickly faked a smile to brush that off.

“Yeah, I’m fine, man. So, um, which movie do you wanna see?”

“I was thinking ‘100 Things’ if it’s okay with you. It’s written by your favorite scriptwriter.”

Dean skimmed over the movie flyer and wasn’t surprised to find out that Cas had been right. As much as Dean enjoyed a good romantic film and he was a sucker for a chick flick, he didn’t feel like watching something like this with Cas. Well, at least not today, since they’d actually watched romantic movies together, before this dating shenanigan. Dean would walk over to the counter with a straight face, asking for two tickets. However, this time, the circumstances were different and he really didn’t want this to end up looking like a real date.

So he randomly picked up another flyer as long as it didn’t seem at all like a romantic genre. “We can watch this, er, ‘The Benders’. Looks fun.”

Cas carefully read through the flyer over before glancing at Dean with uncertainty. “Are you sure you want to watch this one?”

“Why not? I feel like watching horror films today.”

“Alright, then.”

Dean wished desperately that he could go back in time and pick out another movie. Hell, he’d even shut up and just watch ‘100 Things’ with Cas. He was more than okay with gory or bloody scenes because he knew they were all fake anyway. So he assumed that he would be fine watching ‘The Benders’ but he was so wrong. Something was unsettling about this movie and Dean knew exactly why – it was humans that were hunting other people and that made him sick in the stomach.

As soon as the movie ended, Dean bolted outside and took in the fresh air and Cas managed to keep up with him and ask, “Are you okay, Dean?”

“Yeah, I’m fine, I’m fine. It’s just that the movie was... nothing like I was expecting.”

“...I’m sorry.”

A quiet apology was not at all what Dean was expecting and Dean’s head snapped up to meet his gaze. “Why are you saying sorry?”

“I’m sorry that you didn’t like it. I should’ve-”

“Hey, don’t say that. I was the one who picked it.”

“But-“

Cas looked like he wanted to complain but Dean wasn’t about to let him blame himself for something that wasn’t his fault.

“No but. I picked the movie and that means it’s on me if I didn’t like it. Did you find it ok?”

“Yes, it was alright.”

“Good, then at least one of us enjoyed it.” He offered a warm smile at Cas. “Now, where do we go next?”

“The diner.”

“You really are sticking with the classics, aren’t you?” Dean chuckled.

Cas retorted in a teasing voice, “It’s only because my date happens to be a hopeless romantic.”

The dinner was perfect. Not even a bad movie could dampen Dean’s appetite and Dean had a burger, French fries, and a milkshake in his favorite restaurant. Cas had ordered a burger, a salad, and an orange juice and Dean looked at him scandalously for ordering a salad with a burger, which Cas simply shrugged off. Cas got Dean to try a forkful of salad and in return, Dean made Cas try a stick of French fries dipped in a milkshake.

That is why Dean sighed happily, as he finally pulled the car up to the driveway of his home. He has lost the friendly argument between the two of them as to who gets to drop off whom.

When he saw Cas awkwardly trailing behind him, Dean blurted out without thinking, “You know you still haven’t kissed me good night, right?”

“I-I didn’t want to push it.” Color crept up to his cheek as Cas mumbled back.

“Well, if you want to, go ahead. I promise I won’t tease you for being a bad kiss-“

It was almost as if Cas had been waiting for Dean to suggest the idea first because he wasted no time to close the distance between them.

Cas’ gaze flickered to look straight into Dean’s eyes before he slowly tiptoed and pressed his lips to Dean’s.

His lips were warm and soft and he kissed Dean tenderly like a gentleman he always was. This wasn’t something remotely like a kiss in Dean’s standard. Since Cas had never kissed someone before, he didn’t even know that he could use his tongue and Cas just awkwardly kept his lips firmly pressed to Dean’s lips. It was just something you do as kids and Dean would have laughed if he didn’t feel his heart flutter. Because this felt like a confession all over again, except it was without words.

Fuck, he was so fucked. He was in trouble. He wasn’t just falling in love, he might already be in love with Cas.

DAY 6

It was 10 am when he heard his phone ringing. He picked it up too late and the notification let him know that there were 2 missed calls and several unread messages. Two of the messages were from Cas in the night, asking him if everything was alright, and the rest were also from him this morning. Dean sighed and tossed his phone on the bed before dragging his feet to head downstairs.

“Dean, Cas came by like 10 minutes ago. He was worried about you being sick,” Sam yelled, probably because he heard Dean walking down the stairs.

Dean stopped in the midway, ducking his head, and hissed, “Wait, he’s here right now? You didn’t rat me out, did you?”

Sam made a bitch face as he retorted, “Of course not, I sent him away after I reassured him that it was nothing too serious.”

“You’re one smart little guy, you know that?”

Dean ruffled Sam’s hair and Sam tried to stop him. “Hey, stop it!” When Dean finally pulled away, Sam asked curiously, “But why’d you lie to him?”

“It’s complicated. And keep your nose out of my business.”

He tried to brush him off but Sam crossed his arms as he reasoned, “Well, I got more than enough time and I lied to Cas for you. So tell me.”

Dean couldn’t believe that he’s going to have this talk again, with his baby brother nonetheless. So he let out a huge sigh, before beginning to explain what had happened over the past week. Sam was very attentive, nodding every now and then, and Dean realized afterward that he had spilled out everything.

“And you are avoiding him why? What exactly is the problem here?” Sam exclaimed, as soon as Dean finished the story.

“The problem is that I don’t want to like my best friend that way. What if we break up? What then?”

He knew he was acting like a child in front of his younger sibling but he couldn’t bring himself to care. This was an issue for him no matter what others may tell him.

“But you do like him,” Sam pointed out. “And it’s not a bad thing, Dean. Those worries you make, they are just possibilities. Since when were you so worried about the ‘what-if’s anyway?”

Sam frowned at Dean like he was trying to figure out some sort of a complicated math problem and Dean only looked up at the ceiling in annoyance. For a smart kid, he sometimes missed the obvious.

“Since this is Cas we are talking about.”

“Then you got nothing to worry about because he’s not going anywhere. He likes you way too much.”

“Yeah, right,” Dean scoffed, earning a frustrated sigh from Sam.

“I mean it, Dean! He likes you more than anyone else I know. Even more than me.”

Dean jutted his lower lips to fake a pout. “Sam, now that just hurt.”

“What I’m saying is that you are overthinking this. He likes you and you like him back but you’re just focusing on the downside.”

“Well, you would too if you had a best friend for 10 years. Better safe than sorry.”

“Wow, I never thought you’d say that-” Dean sent an evil glare toward Sam’s direction and Sam raised his hand in mock surrender. “Fine, you know what? I’m going to ‘keep my nose out of this’. But before you decide on anything, talk to Cas. He’s your friend, Dean. Besides, you complained about Cas hiding his feelings until now and yet you’re doing the exact same thing.”

“I know.”

Sam’s face softened as he sighed, “It’s just... Cas deserves to know this and I promise it’s better if you guys talk this out, okay?”

“Okay,” Dean answered grudgingly before he added teasingly, “Although I don’t think you should be the one giving advice. I mean, how many times did you go out on a date? Oh, that’s right, none.”

“Jerk, it’s not like you are any better – even though you went out on dates.”

“Bitch.”

Talking about it was one thing, but actually following the advice was another. Dean wasn’t sure what would await him tomorrow and he sure as hell wasn’t ready for it but tomorrow he’d talk about it. With Cas.

DAY 7

Dean had texted Cas yesterday evening telling him that he felt better. Knowing Cas, he’d probably show up first thing in the morning so today Dean woke up early. Although it was Sunday. However, he was completely wrong and Cas had only sent him a message which said he would come over around 8 in the evening. Dean was tempted to walk up to Cas’ house and invited himself over but he didn’t want to risk having Naomi – no, Ms. Novak – opening the door. She would undoubtedly strike up a conversation with him and he really didn’t have the energy to keep up with her prying questions today.

He decided that he has some time to kill and picked up a book he had borrowed from Charlie. It was the same book that he had read Tuesday but to be honest, he no longer remembered what the book was about. Well, he had all the time in the world anyway.

With each tick of the second hand, Dean felt his anxiety growing and about half an hour later he noticed that he had been reading the same page. He huffed a sigh and slapped the book close, before pacing back and forth, only to pause when he groaned to himself or bothered Sam.

It was almost exactly 8 o’clock when Cas texted him that he was at the front porch. Dean ran downstairs, ignoring the questions from his parents and a knowing glance from Sam, and opened the door.

The tip of Cas’ nose was slightly red and Dean had a growing suspicion that Cas might have been standing in front of the door for a while. Nonetheless, he pushed that thought aside and grinned at him.

“Hey, Cas.”

“Hello, Dean.” His lips were curved into a soft smile but they quickly turned into a grimace, as he murmured, “So today is the end of our one-week arrangement.”

Ah, cutting to the chase. Dean felt his words pricking at his poor heart but he managed to keep his voice light when he replied, “And you’re ok with that?”

“I got what I asked.” That sounded almost bitter and Dean tried to look into his friend’s eyes, who quickly turned his head away. “But don’t worry, Dean. I don’t plan to make this awkward for you. I am ready to move on.”

That made Dean bristle and he couldn’t help but burst out with, “Just like that? You can just snap your finger and decide that you wanna date me but snap again and you are back to being my friend?”

Cas tilted his head to the left and stared at him quizzically. “You seem angry, Dean. What are you so angry about?”

“Oh, I don’t know, Cas. Why did you start all this, if you can just turn your feelings on and off? Like, what’s the whole point?”

If Dean could shoot dagger with his eyes, he would. Because every word that was coming out of Cas’ mouth was hurting him.

“I’m sorry.” He spoke in such soft whisper that Dean almost missed it.

“So you’re sorry. Is that it?”

Cas’ eyes flashed with an emotion Dean didn’t know what to call it but before Dean could say something, Cas laughed bitterly.

“What else should I say then, Dean? That ever since I can remember, all my life I’ve always orbited around you without really knowing why? And when I realized I was in love with my best friend, I also knew this feeling would never be reciprocated?”

His chest tightened, almost aching because he didn’t know half of the things Cas just told him and he could only imagine what that must have been like.

With a catch in his voice, he talked lowly, “...Why didn’t you say something?”

“Since I was happy as long as you were. That’s why I would have never confessed to you, except you seemed so unhappy with all your past dates and I wanted you to see how easily we already fit into our lives, how nothing would have to change and... that maybe I am the one who understands you the most.“

“Cas.”

Dean felt his voice trembling but Cas looked up at him with an equally wobbly smile.

“I like you too, you know.”

“You, you like me? Do you mean-”

Hearing Cas’ breathless voice made Dean feel a little bit more confident.

“Yes, in a romantic sense. I think I liked you more than I realized.”

“Oh.”

“Yeah, so we were just a couple of dumbasses.”

Cas frowned slightly in disapproval but his expression was warm as he argued, “I prefer the word ‘careful’. Less dumb, less ass.” Dean let out a laugh, unable to control himself, and Cas looked puzzled. “What?”

“Nothing! I am laughing because my boyfriend is such a weird, dorky little guy.” Seeing Cas’ expression turn blank, panic began to rise in Dean and he fumbled, “Or maybe you don’t want-“

His sentence was cut off when Cas hugged him tightly and smiled, “No, I’d like that very much.”

“Great! I mean, yeah, cool.” Dean mentally kicked himself for sounding so stupid changed the topic to ask, “Wanna come inside?”

“No, I’m going back home soon.”

“Then you want me to come with you? After all, you are still hugging me.”

Dean laughed again when he saw how reluctantly Cas pulled away from him. He would be lying if he didn’t feel the same.

“No, not today,” Cas replied, shaking his head lightly, before offering Dean a warm smile. “I’ll see you tomorrow, Dean.”

“Yeah, see you.”

Dean watched Cas walk away and that took a while since Cas stopped to turn around and look at him like he missed him already. Once Cas was at the front porch of his house, did Dean finally head back inside. He ran back up the stairs to his room and closed the door, only to lean against it and pump his fist up in the air.

He couldn’t wait to see Charlie’s face tomorrow.

**Author's Note:**

> Icons made by [Darius Dan](https://www.flaticon.com/authors/darius-dan) from [www.flaticon.com](https://www.flaticon.com/)


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